Relax and use lube. Lots and lots of lube, and then some more lube. As pleasurable as anal sex can be, it can also hurt like nothing else on earth if you get it wrong. And if that isn’t bad enough, you can also end up doing some real damage to your rectum if you aren’t careful.
In order for anal sex to be safe, you must be sober and lucid so you can pay attention to the signs that your body is giving you. You should expect to feel a minimal amount of discomfort since your rectum isn’t made to lubricate and stretch the way a vagina is, but if it there is any real pain it’s a sign that you need to stop and regroup.
Your relaxation and comfort is an absolute must. You won’t get anything past your sphincter if you are clenching those muscles, at least not without extreme pain and severe damage. Take deep breaths and release the tension down there. In order for this part to work, you need to trust your partner and have total confidence that he’ll allow you to set the pace.
Talk to him before you even begin, and let him know that you need to be in control. Find a position* where you are comfortable and where gravity will not work to drive his penis into you. Ask him to refrain from pushing his penis into you, instead allowing you to back yourself on to him; it’s the best way to ensure that he won’t move too deep too fast.
Most of the resistance during vaginal sex is felt during the initial penetration, but your rectum needs gradual stretching all the way in. Rock back and forth on his penis, allowing it to enter a millimeter more each time. If you move too fast it will hurt, and if it hurts, you will clench – and that will only increase your pain to the point where you need to give up.
You may never feel comfortable taking his entire length, and that’s okay – your partner can still enjoy the activity. Once you have taken him in as far as you want – with those little rocking motions – you can gradually increase the pace or even allow him to take over control – but only if you trust him to respect your request not to push in any deeper than you’ll allow, and to follow the tempo you’ve set.
Before his penis even approaches your anus, you will need to ask him to finger you while applying lube. Think about how much lubrication you’d need to shove a tennis ball through a keyhole, and then double that. Make sure you get the lube inside you, all around your anus, and on the entire length of his penis.
Ask him to use his fingers to periodically apply more around your hole, both while you are rocking your way onto him and once you start going at it. He will likely have a hard time understanding just how much lube you need, and how frequently you’ll need it reapplied, so make sure that he knows what to do whenever you say “more lube”. He might be worried that it will get too slippery, so go ahead and reassure him that not even a swimming pool full of lube could take away the very tight friction of anal sex.
It sounds complicated, I know, but it will get easier when you learn to relax and figure out your limits. You can have very pleasurable receptive anal sex, whether you’re male or female, but it’s one of those things that you have to get right. You know how some foods can still be pretty good even if they’re bad? Anal sex is not like that.
